caser

Ha, author here -- I'm probably a member of this group myself. I bootstrapped my first company and then ran a small consultancy for awhile.

Spent some time at a fund, but we primarily bought and operated SaaS companies as cash flow businesses. It's been base hits all the way.

I think if you're happy with building a business that gives you freedom and work life balance, this can be a great life. Personally, I eventually got tired of consulting even though it was good money and lifestyle. There were other things I wanted to work on that I didn't have time for, and I wanted to create something of my own, rather than just working on other people's projects.

But that's just my experience--I think if you're happy in the freelance / agency life, it can be great, but you are still ultimately selling time for money. Maybe this is a 4th path, the career craftsman--working a job you enjoy with people you like, and not needing your work to be as aligned with a "passion" or some sort of calling.

Just my $0.02 -- appreciate the comment and will have to make my writing sound less like an AI in the future ^_^;;

Yep -- this is where I tend to see people end up after doing a sabbatical. That, or they alternate between periods of highly paid work and periods bumming skydiving, making art, etc.

Hey, author of the post here. My takeaway after trying all these strategies is that there's no one right answer. All paths can work but also have failure states.

If you want to talk, feel free to drop me a note - [email protected]. I spent 2 years doing consulting before shifting into other work, happy to share more specific thoughts / reflections offline.